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The room temperature preparation of the 1-chloro-2,2-difluorovinylzinc reagent from HCFC-133a (CF3CH2Cl). The first ambient, high yield, one-flask preparation of α-chloro-β,β-difluorostyrenes

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
39
Identifiers
DOI: 10.1016/s0040-4039(02)01591-5
Keywords
  • Hcfc-133A
  • Chlorodifluorovinylzinc
  • Pd(0) Coupling
  • Chlorodifluorovinyllithium
  • α-Chloro-β
  • β-Difluorostyrene

Abstract

Abstract The reaction of LDA (2.0 equiv.) with a THF solution of ZnCl 2 (1.0 equiv.) and HCFC-133a (CF 3CH 2Cl) (1.0 equiv.) at 15–20°C gives a 91% yield of [F 2CCClZnCl]. Addition of ArI and Pd(PPh 3) 4 at rt to 65°C gives 65–85% isolated yields of ArCClCF 2. This one-flask procedure provides the first room temperature generation of the 1-chloro-2,2-difluorovinylzinc reagent and the first high yield preparation of α-chloro-β,β-difluorostyrenes from a cheap, readily available industrial precursor.

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